Palladium‐Templated Subcomponent Self‐Assembly of Macrocycles, Catenanes, and Rotaxanes

Browne, Colm; Ronson, Tanya K.; Nitschke, Jonathan R.

doi:10.1002/ange.201406164

Cited by 14 publications

(2 citation statements)

References 57 publications

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“…Nitschke and coworkers have also reported a recent 1,3 system using imine coordination chemistry. The 1 : 1 : 1 combination of 2,6-diformylpyridine and benzidine with Pd II in acetonitrile gave rise through imine condensation to an equilibrium mixture of tris-tridentate (L28) [47] and tetra-tridentate (L29) macrocycles, [Pd 3 L28(CH 3 CN) 3 ] 6 + and [Pd 4 L29 (CH 3 CN) 4 ] 8 + (Figure 19). [45] They sought to induce quantitative product formation using appropriate poly-monodentate ligands as central templates.…”

Section: 3 Assembliesmentioning

confidence: 99%

Cover Feature: (ChemPlusChem 5/2020)

Preston

Kruger

2020

ChemPlusChem

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The Cover Feature shows a jigsaw with some of the structures discussed in this Minireview. This overview details two of the less‐explored arrangements of ligands around square‐planar metal ions, and how they can be used to assemble exciting metallosupramolecular architectures. The Lego bricks symbolize the construction of complex structures from simple componentry. More information can be found in the Minireview by D. Preston and P. Kruger (DOI: 10.1002/cplu.202000019). The authors thank the Lego Group for allowing them to include the bricks in this image.

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Section: 3 Assembliesmentioning

confidence: 99%

Cover Feature: (ChemPlusChem 5/2020)

Preston

Kruger

2020

ChemPlusChem

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“…Nitschke and coworkers have also reported a recent 1 , 3 system using imine coordination chemistry. The 1 : 1 : 1 combination of 2,6‐diformylpyridine and benzidine with Pd II in acetonitrile gave rise through imine condensation to an equilibrium mixture of tris ‐tridentate ( L28 ) and tetra ‐tridentate ( L29 ) macrocycles, [Pd 3 L28 (CH 3 CN) 3 ] 6+ and [Pd 4 L29 (CH 3 CN) 4 ] 8+ (Figure ) . They sought to induce quantitative product formation using appropriate poly‐ monodentate ligands as central templates.…”

Section: Introductionmentioning

confidence: 99%

Using Complementary Ligand Denticity to Direct Metallosupramolecular Structure about Metal Ions with Square‐Planar Geometry

Preston

Kruger

2020

ChemPlusChem

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An understanding of methods to control the structure of self‐assembled architectures is central to the efforts of chemists interested in self‐assembly synthesis. Metal ions with square‐planar geometry are a favorite of metallosupramolecular chemists, as there are only a limited number of possible ligand arrangements around the metal ion. Two such arrangements, firstly four monodentate donor sites (1,1,1,1), and secondly two monodentate donors and one bidentate donor (1,1,2) exemplify the symmetry interaction and ligand directed approaches, respectively. Symmetry interaction approaches using two bidentate sites (2,2) or a monodentate and tridentate site (1,3) have not received the same level of attention. In these arrangements, two complementary sites combine at the metal ion(s). This Minireview seeks to detail strategies employed to direct structure in systems with these arrangements, and is illustrated with key exemplars from the field.

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A Simple and Highly Effective Ligand System for the Copper(I)‐Mediated Assembly of Rotaxanes

et al. 2014

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A [2]rotaxane was produced through the assembly of a picolinaldehyde, an amine, and a bipyridine macrocycle around a Cu I template by imine bond formation in close-toquantitative yield. An analogous [3]rotaxane is obtained in excellent yield by replacing the amine with a diamine, thus showing the suitability of the system for the construction of higher order interlocked structures. The rotaxanes are formed within a few minutes simply through mixing the components in solution at room temperature and they can be isolated through removal of the solvent or precipitation.The Copper(I) template system based on 2,9-diphenyl-1,10-phenanthroline (dpp) ligands, [1] introduced by Sauvage and co-workers in the 1980s, [2] revolutionized the synthesis of catenanes, rotaxanes, and knots [3] and has remained a mainstay of interlocked molecule synthesis for three decades.[4] In the early years, the covalent capture of the threaded intermediates was often carried out through Williamson ether synthesis, [2,5] but ring-closing olefin metathesis [6] and CuAAC click chemistry [7] have proved to be effective methods of choice in recent times.[3] Imine bond formation is a particularly attractive reaction for preparing interlocked molecules; [8] it occurs under mild conditions and its reversible nature allows error-checking during the assembly process, particularly when combined with metal ion coordination.[9]Herein, we describe a ligand set featuring a bipyridyl macrocycle and a 2-pyridylimine axle assembled around Cu I to form threaded molecular structures in close-to-quantitative yields. [10,11] The system is a simple-to-access, high yielding version of the traditional Sauvage interlocking ligand system. Upon mixing equimolar quantities of solutions of bipyridyl macrocycle 1, picolinaldehyde 2, amine 3, and Cu-(MeCN) 4 PF 6 in MeCN at room temperature (Scheme 1), the solution immediately turns dark red.1 H NMR spectroscopy (Figure 1 b) and mass spectrometry (see the Supporting Information) of the reaction mixture indicate that a single species, [2]rotaxane 4, is assembled almost quantitatively within five minutes at room temperature (significantly faster than imine-based rotaxane formation with octahedral metal templates [8d] ). The use of other solvents, including CH 2 Cl 2 , CHCl 3 , DMF, MeOH, and THF, also give high (typically

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Palladium‐Templated Subcomponent Self‐Assembly of Macrocycles, Catenanes, and Rotaxanes

Cited by 14 publications

References 57 publications

Cover Feature: (ChemPlusChem 5/2020)

Cover Feature: (ChemPlusChem 5/2020)

Using Complementary Ligand Denticity to Direct Metallosupramolecular Structure about Metal Ions with Square‐Planar Geometry

A Simple and Highly Effective Ligand System for the Copper(I)‐Mediated Assembly of Rotaxanes

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